Shelter Island Hotel Guide - Hotels with Pool in Shelter Island, New York
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28 Aug - 30 AugOur top choices for Shelter Island hotels with a pool
1. Work and Play Special! Extended Stay Discount
Work and Play Special! Extended Stay DiscountShelter Island
€1,178
includes taxes & fees
17 Sept - 18 Sept
2. Shelter Island House
Shelter Island HouseShelter Island Heights
- Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
€312
includes taxes & fees
17 Sept - 18 Sept
3. The Harbor Front Inn
The Harbor Front InnGreenport
- Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
€317
includes taxes & fees
8 Sept - 9 Sept
4. West Neck Guesthouse
West Neck GuesthouseShelter Island Heights
- Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
€309
includes taxes & fees
17 Sept - 18 Sept
5. Sound View Greenport
Sound View GreenportGreenport
- Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
€342
includes taxes & fees
15 Sept - 16 Sept
€317
includes taxes & fees
7 Sept - 8 Sept
7. The Pridwin Hotel
The Pridwin HotelShelter Island Heights
- Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
€580
includes taxes & fees
14 Sept - 15 Sept
8. Cliffside Resort Condominiums
Cliffside Resort CondominiumsGreenport
- Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
€379
includes taxes & fees
7 Sept - 8 Sept
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Top Shelter Island Hotel Reviews
Water's Edge Resort & Spa
8/10 Good
"I booked through Expedia because I believed the price I was quoted would be the final cost other than incidentals. Additional resort fees and tax were added to the final bill. Over 130.00 in unexpected cost. Be aware when booking."
Kenny's Tipperary Inn
10/10 Excellent
"Very clean rooms and pet friendly! Good location"
Hampton's Vacation Inn
10/10 Excellent
"Great place to stay. The closing of the pool at 7pm is a bit early."
Sound View Greenport
10/10 Excellent
"Hotel very well situated with a nice beach and a great pool. The rooms were clean and spacious. There were a lot of families so we couldn’t just sit and enjoy the view with toddlers running around - but that was me 20 years ago. I would recommend but next time I would want to book the private patio rooms. Continental breakfast was great - all around fantastic stay."
Ocean Resort Inn
10/10 Excellent
"It was a great stay!"